Dimethylformamide → 2-Chloro-N-{1-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247501ノート

反応式

HRID 1247501 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]([NH:22][C:23]([C:25]2[NH:29][C:28]3[S:30][C:31]([Cl:33])=[CH:32][C:27]=3[CH:26]=2)=[O:24])[C:13]1=[O:34])(O)=[O:9].CCN=C=NCCCN(C)C.CN(C=O)C>CN(C)C1C=CN=CC=1.C1COCC1.O>[Cl:33][C:31]1[S:30][C:28]2[NH:29][C:25]([C:23]([NH:22][CH:14]3[CH2:15][C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:12]([CH2:11][C:8]([N:5]4[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]4)=[O:9])[C:13]3=[O:34])=[O:24])=[CH:26][C:27]=2[CH:32]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 79341Piperidin-4-olHCID 10319016N-[1-(Carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

生成物 1

HCID 100969462-Chloro-N-{1-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide収率 59%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

4-Dimethylaminopyridine (5 mg, 0.038 mmol) and 4-hydroxypiperidine (42 mg, 0.41 mmol) were added to a suspension of N-[1-(carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 2; 150 mg, 0.38 mmol) and EDCI (79 mg, 0.41 mmol) in THF (0.5 mL) under an inert atmosphere. DMF (0.5 mL) was added and the mixture stirred at ambient temperature for 18 h. After pouring into water (10 mL) the resultant solid was filtered off and washed with 1M HCl aq. and water. Chromatography on silica gel (eluent gradient of CH2Cl2 to MeOH:CH2Cl2 (1:9)) afforded the title compound (109 mg, 59%) as an off white solid.

後処理

  1. filtrationwas filtered off
  2. washwashed with 1M HCl aq. and water

出典と根拠

ORDレコード
ord-58b6a31d3a7e4952a59b5a823c0d804a
出典データセット
uspto-grants-2006_10
特許番号
US07129249B2

反応ノート

読み込み中…